Phenyl isocyanate → HCID 10118654, compound

HRID 970916Notes

Reaction equation

HRID 970916 reaction equation
[NH2:1][CH2:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]([CH2:19][C:20]2[NH:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[N:21]=2)[CH:9]2[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:31]1([N:37]=[C:38]=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[NH:24]1[C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[N:21]=[C:20]1[CH2:19][N:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:38]([NH:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:39])=[CH:30][CH:29]=1)[CH:9]1[C:18]2[N:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 10118654HCID 10118654, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of (4-aminomethyl-benzyl)-(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.136 g, 0.34 mmol) in CH2Cl2 (3.5 mL) was added phenyl isocyanate (41 μL, 0.38 mmol) and the resultant solution was stirred for 50 minutes. The cooling bath was removed and the mixture was concentrated under reduced pressure. Purification of the crude material by column chromatography on silica gel (25:1:1 CH2Cl2—CH3OH—NH4OH) provided the free base of the title compound (0.127 g, 72%) as a white solid.

Workup

  1. customThe cooling bath was removed
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customPurification of the crude material by column chromatography on silica gel (25:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-31bbc27be5ad4878bcabfd04876b6bbc
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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